#------------------------------------------------------------------------------
#$Date: 2017-04-04 15:21:09 +0200 (mar 04 de abr de 2017) $
#$Revision: 194854 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/21/4032195.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4032195
loop_
_publ_author_name
'Wang, Wenhui'
'Han, Junwen'
'Sun, Jinwei'
'Liu, Yun'
_publ_section_title
;
 CuBr-Catalyzed Aerobic Decarboxylative Cycloaddition for the Synthesis of
 Indolizines under Solvent-Free Conditions.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2835
_journal_page_last               2842
_journal_paper_doi               10.1021/acs.joc.6b02455
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C18 H14 Cl N O3'
_chemical_formula_weight         327.75
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.325(7)
_cell_angle_beta                 97.507(7)
_cell_angle_gamma                97.595(7)
_cell_formula_units_Z            2
_cell_length_a                   7.517(3)
_cell_length_b                   9.801(4)
_cell_length_c                   11.650(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     765.3(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4237
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0597P)²+0.1148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                2096
_reflns_number_total             2655
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02455_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 4032195.cif.'
_cod_original_cell_volume        765.3(6)
_cod_database_code               4032195
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.33378(10) 1.15387(7) 0.05842(6) 0.0798(3) Uani 1 1 d .
N1 N 0.2215(2) 0.60010(16) 0.42538(14) 0.0414(4) Uani 1 1 d .
C13 C 0.2200(2) 0.5920(2) 0.62913(17) 0.0423(4) Uani 1 1 d .
H13 H 0.2056 0.6367 0.7133 0.051 Uiso 1 1 calc R
C16 C 0.2598(3) 0.4561(2) 0.37730(19) 0.0487(5) Uani 1 1 d .
H16 H 0.2723 0.4099 0.2928 0.058 Uiso 1 1 calc R
O3 O 0.2760(2) 0.44279(16) 0.78035(14) 0.0608(4) Uani 1 1 d .
C14 C 0.2609(2) 0.4509(2) 0.58193(18) 0.0440(5) Uani 1 1 d .
O2 O 0.3227(3) 0.23999(17) 0.62025(15) 0.0724(5) Uani 1 1 d .
C12 C 0.1995(2) 0.66985(19) 0.55199(17) 0.0410(4) Uani 1 1 d .
C15 C 0.2788(3) 0.3835(2) 0.45292(19) 0.0490(5) Uani 1 1 d .
H15 H 0.3042 0.2866 0.4199 0.059 Uiso 1 1 calc R
C6 C 0.3909(3) 1.0346(2) 0.22816(19) 0.0510(5) Uani 1 1 d .
H6 H 0.4743 1.1249 0.2781 0.061 Uiso 1 1 calc R
C8 C 0.2049(3) 0.6998(2) 0.37010(17) 0.0450(5) Uani 1 1 d .
C7 C 0.2124(3) 0.6618(2) 0.23792(18) 0.0508(5) Uani 1 1 d .
C17 C 0.2894(3) 0.3651(2) 0.6602(2) 0.0498(5) Uani 1 1 d .
C5 C 0.3612(3) 0.9235(2) 0.27169(18) 0.0500(5) Uani 1 1 d .
H5 H 0.4234 0.9398 0.3519 0.060 Uiso 1 1 calc R
O1 O 0.1965(3) 0.52995(17) 0.15942(13) 0.0709(5) Uani 1 1 d .
C10 C 0.1634(3) 0.8135(2) 0.57394(17) 0.0438(5) Uani 1 1 d .
C4 C 0.2391(3) 0.7875(2) 0.19700(17) 0.0470(5) Uani 1 1 d .
C11 C 0.1235(3) 0.9239(2) 0.69472(18) 0.0538(5) Uani 1 1 d .
H11A H 0.1147 1.0173 0.6879 0.081 Uiso 1 1 calc R
H11B H 0.2204 0.9426 0.7648 0.081 Uiso 1 1 calc R
H11C H 0.0098 0.8826 0.7091 0.081 Uiso 1 1 calc R
C9 C 0.1697(3) 0.8311(2) 0.46292(17) 0.0462(5) Uani 1 1 d .
H9 H 0.1530 0.9175 0.4513 0.055 Uiso 1 1 calc R
C3 C 0.1488(3) 0.7652(2) 0.07710(18) 0.0556(5) Uani 1 1 d .
H3 H 0.0697 0.6732 0.0250 0.067 Uiso 1 1 calc R
C1 C 0.2963(3) 1.0111(2) 0.11023(19) 0.0535(5) Uani 1 1 d .
C2 C 0.1748(3) 0.8772(3) 0.03434(19) 0.0587(6) Uani 1 1 d .
H2 H 0.1109 0.8625 -0.0449 0.070 Uiso 1 1 calc R
C19 C 0.3032(4) 0.3687(3) 0.8638(2) 0.0709(7) Uani 1 1 d .
H19A H 0.2111 0.2778 0.8336 0.106 Uiso 1 1 calc R
H19B H 0.2945 0.4354 0.9485 0.106 Uiso 1 1 calc R
H19C H 0.4222 0.3432 0.8653 0.106 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 C16 130.75(16)
C8 N1 C12 108.59(14)
C16 N1 C12 120.61(16)
C14 C13 C12 120.51(17)
C15 C16 N1 119.69(17)
C17 O3 C19 116.21(17)
C13 C14 C15 118.99(18)
C13 C14 C17 122.86(17)
C15 C14 C17 118.15(17)
C13 C12 C10 133.28(17)
C13 C12 N1 118.69(16)
C10 C12 N1 108.01(16)
C16 C15 C14 121.49(18)
C5 C6 C1 119.58(19)
N1 C8 C9 106.75(17)
N1 C8 C7 123.18(16)
C9 C8 C7 129.95(19)
O1 C7 C8 122.13(19)
O1 C7 C4 119.74(18)
C8 C7 C4 118.13(16)
O2 C17 O3 123.7(2)
O2 C17 C14 124.02(19)
O3 C17 C14 112.30(17)
C6 C5 C4 120.58(19)
C9 C10 C12 106.71(16)
C9 C10 C11 127.38(18)
C12 C10 C11 125.91(18)
C5 C4 C3 118.71(19)
C5 C4 C7 121.85(18)
C3 C4 C7 119.30(17)
C10 C9 C8 109.91(18)
C2 C3 C4 120.93(19)
C2 C1 C6 120.9(2)
C2 C1 Cl1 120.34(17)
C6 C1 Cl1 118.72(16)
C1 C2 C3 119.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.735(2)
N1 C8 1.376(3)
N1 C16 1.383(2)
N1 C12 1.402(2)
C13 C14 1.365(3)
C13 C12 1.397(3)
C16 C15 1.339(3)
O3 C17 1.328(2)
O3 C19 1.436(3)
C14 C15 1.415(3)
C14 C17 1.480(3)
O2 C17 1.201(2)
C12 C10 1.398(3)
C6 C5 1.376(3)
C6 C1 1.377(3)
C8 C9 1.400(3)
C8 C7 1.445(3)
C7 O1 1.231(2)
C7 C4 1.486(3)
C5 C4 1.388(3)
C10 C9 1.377(3)
C10 C11 1.494(3)
C4 C3 1.389(3)
C3 C2 1.376(3)
C1 C2 1.376(3)
